GB905099A - Method of manufacturing cis-1,4-polybutadiene - Google Patents

Method of manufacturing cis-1,4-polybutadiene

Info

Publication number
GB905099A
GB905099A GB44576/60A GB4457660A GB905099A GB 905099 A GB905099 A GB 905099A GB 44576/60 A GB44576/60 A GB 44576/60A GB 4457660 A GB4457660 A GB 4457660A GB 905099 A GB905099 A GB 905099A
Authority
GB
United Kingdom
Prior art keywords
catalyst
organic
component
boron
polybutadiene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB44576/60A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bridgestone Corp
Original Assignee
Bridgestone Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bridgestone Corp filed Critical Bridgestone Corp
Publication of GB905099A publication Critical patent/GB905099A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F136/06—Butadiene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Polybutadiene having a high cis-1,4 configuration is made by polymerizing butadiene in the liquid state in the presence of a three component catalyst comprising (A) an organic acid salt of nickel or cobalt in which the organic acid is selected from organic carboxylic, organic thiocarboxylic, organic dithiocarboxylic, and organic sulphonic acids or substituted acids thereof, (B) a compound selected from chlorides and oxychlorides of the metals of Group IV(a) and V(a) of the Mendel<\>aeeff Periodic Table, and boron halides and complexes, and (C) a substance selected from organometallic compounds and hydrides of metals of Group I, II and III of the Periodic Table, and alkali-metal powders. The (A) component of the catalyst may be nickel formate, acetate, naphthenate, benzoate, palmitate, octenate, palmitate, stearate, oxalate, ethylbenzoate, ethathiolate, ethantionate, ethanthionthiolate, thiobenzoate, dithiobenzoate, dialkyldithiocarbonate, ethylsulphonate, propylsulphonate, butylsulphonate, benzenesulphonate, benzene metadisulphonate, p-toluyl-sulphonate, cyclohexanesulphonate, p-toluidine-m-sulphonate, and the corresponding cobalt salts. The (B) component of the catalyst may be titanium, zirconium, or vanadium tetrachloride, zirconium oxydichloride, vanadium oxytrichloride, vanadium trichloride, boron trifluoride, boron trichloride, boron tribromide, or the ether component of the catalyst may be selected from triethyl-, tributyl-, triisobutyl-, triphenyl-aluminium, tributylboron, diethylmagnesium, diethyl zinc, diethylcadmium, butyllithium, cyclohexyllithium, lithium aluminium tetrabutyl, lithium aluminium hydride, lithium hydride, sodium hydride, and metallic lithium. The catalyst is performed by admixing the three components in an anhydrous liquid hydrocarbon diluent. The polymerization is generally effected in bulk, e.g. in the liquid monomer, if desired, solvents such as benzene, toluene, xylene, pentane, butane, and diisopropyl ether, may also be present. The polybutadiene may be recovered and purified by known techniques. Specification 846,731 is referred to.
GB44576/60A 1959-12-31 1960-12-29 Method of manufacturing cis-1,4-polybutadiene Expired GB905099A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP4151859 1959-12-31
JP2618060 1960-06-01

Publications (1)

Publication Number Publication Date
GB905099A true GB905099A (en) 1962-09-05

Family

ID=26363927

Family Applications (1)

Application Number Title Priority Date Filing Date
GB44576/60A Expired GB905099A (en) 1959-12-31 1960-12-29 Method of manufacturing cis-1,4-polybutadiene

Country Status (4)

Country Link
US (1) US3170907A (en)
DE (2) DE1213120B (en)
FR (1) FR1283371A (en)
GB (1) GB905099A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3234198A (en) * 1962-12-10 1966-02-08 Shell Oil Co Polymerization process
DE1253918B (en) * 1964-06-06 1967-11-09 Japan Synthetic Rubber Co Ltd Process for the production of cis-1,4-polybutadiene
DE1268394B (en) * 1964-04-30 1968-05-16 Huels Chemische Werke Ag Process for the preparation of mixtures of structurally uniform, high molecular weight 1,4-cis- and 1,4-trans-polybutadienes
DE1570293B1 (en) * 1965-07-13 1970-02-05 Bridgestone Tire Co Ltd Process for making copolymers of conjugated diolefins
DE1570827B1 (en) * 1964-12-07 1970-08-06 Internat Synthetic Rubber Comp Process for the preparation of cis-1,4-polybutadiene
DE2364805A1 (en) * 1972-12-27 1974-08-08 Sumitomo Chemical Co LIQUID SERVICE POLYMERIZES, PROCESS FOR THEIR PRODUCTION AND THEIR USE

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1059877A (en) * 1965-01-18 1967-02-22 Internat Synthetic Rubber Comp Novel catalyst composition for the manufacture of rubbery ethylene copolymers
NL132157C (en) * 1965-10-27
US3438958A (en) * 1967-02-23 1969-04-15 Goodyear Tire & Rubber Method of polymerizing butadiene by means of a reaction product of organoaluminum fluoride,certain organonickel compounds and boron trifluoride or its stable complexes
US3528957A (en) * 1967-07-10 1970-09-15 Goodyear Tire & Rubber Method of producing polybutadiene
US3528953A (en) * 1967-10-10 1970-09-15 Goodyear Tire & Rubber Trialkyl tin fluorides as catalyst additives in butadiene polymerization
US3513149A (en) * 1967-12-11 1970-05-19 Phillips Petroleum Co Gel reduction in cis-polybutadiene process
US3487063A (en) * 1967-12-15 1969-12-30 Goodyear Tire & Rubber Method of polymerizing butadiene or butadiene in mixture with other diolefins
US3483177A (en) * 1967-12-15 1969-12-09 Goodyear Tire & Rubber Method for the polymerization of butadiene and butadiene in mixture with other diolefins using (1) organometallics,(2) organic ni or co,and (3) bf3 complexed with aldehydes,ketones,esters and nitriles
US3542751A (en) * 1969-04-09 1970-11-24 Goodyear Tire & Rubber Production of cis-1,4-polydienes by means of a ternary catalyst system
US4127710A (en) * 1974-10-02 1978-11-28 Phillips Petroleum Company Copolymerization of a 1,3-cyclodiene and a linear conjugated diene
US4020255A (en) * 1975-05-07 1977-04-26 The Goodyear Tire & Rubber Company Continuous insitu catalyst addition for polybutadiene polymerization
US3985941A (en) * 1975-05-12 1976-10-12 The Goodyear Tire & Rubber Company Method of polymerization
US4383097A (en) * 1981-08-21 1983-05-10 The Goodyear Tire & Rubber Company Molecular weight regulation of cis-1,4-polybutadiene
ZA832555B (en) 1982-04-26 1983-12-28 Goodyear Tire & Rubber Controlling the molecular weight of polybutadiene
US4562171A (en) * 1984-06-04 1985-12-31 The Firestone Tire & Rubber Company Method of preparing high cis-1,4 diene polymers having good green strength and tack using a catalyst composition containing a carboxylated metal oxy aluminate component
US4522988A (en) * 1984-06-04 1985-06-11 The Firestone Tire & Rubber Company Method of preparing high cis-1,4 diene polymers having good green strength and tack
US4562172A (en) * 1984-06-04 1985-12-31 The Firestone Tire & Rubber Company Method of preparing high cis-1,4 diene polymers having good green strength and tack
US4522989A (en) * 1984-06-04 1985-06-11 The Firestone Tire & Rubber Company Method of preparing high cis-1,4 diene polymers having good green strength and tack using a catalyst composition containing a carboxylated metal oxy aluminate component
US4501866A (en) * 1984-07-23 1985-02-26 The Firestone Tire & Rubber Company Continuous method for preparing high cis-1,4 polybutadiene
US5412045A (en) * 1994-09-16 1995-05-02 Polysar Rubber Corporation Preparation of high cis-1,4-polybutadiene with reduced gel
US7585805B2 (en) * 2005-11-22 2009-09-08 Bridgestone Corporation Nickel-based catalyst composition
US8372925B2 (en) * 2007-04-10 2013-02-12 Bridgestone Corporation Nickel-based catalyst composition
US7820580B2 (en) * 2007-11-15 2010-10-26 Bridgestone Corporation Nickel-based catalysts for preparing high cis 1,4-polydienes
JP5674651B2 (en) * 2008-06-20 2015-02-25 株式会社ブリヂストン Catalyst for preparing cis 1,4-polydiene
BR112013016429B1 (en) 2010-12-31 2020-12-08 Bridgestone Corporation mass polymerization of conjugated dienes using a nickel-based catalyst system
CN103328519A (en) 2010-12-31 2013-09-25 株式会社普利司通 Bulk polymerization of conjugated dienes using nickel-based catalyst system
CN103596997B (en) 2011-05-09 2016-08-24 株式会社普利司通 For the method preparing high-cis polydiene
US10066035B2 (en) 2015-12-07 2018-09-04 Bridgestone Corporation Catalyst systems and methods for preparation of 1,4-polybutadiene rubber

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2521022A (en) * 1946-05-31 1950-09-05 Interchem Corp Synthetic hydrocarbon resins
US3094514A (en) * 1958-02-13 1963-06-18 Goodrich Gulf Chem Inc Polymerization process for aliphatic, conjugated dienes
US2882264A (en) * 1955-10-10 1959-04-14 Dow Chemical Co Polymerization of ethylene
US2965626A (en) * 1956-03-28 1960-12-20 Standard Oil Co Ethylene polymerization process
US2953554A (en) * 1956-08-07 1960-09-20 Goodrich Gulf Chem Inc Method of removing heavy metal catalyst from olefinic polymers by treatment with an aqueous solution of a complexing agent
US2977349A (en) * 1956-11-07 1961-03-28 Goodrich Gulf Chem Inc Process for polymerizing dienes
US2964627A (en) * 1957-07-01 1960-12-13 Trub Tauber & Co A G Double-focussing spectrometer for electrically charged particles
US2970134A (en) * 1957-11-18 1961-01-31 Shell Oil Co Diene polymerization
NL233912A (en) * 1957-12-06
BE578156A (en) * 1958-04-29
NL240204A (en) * 1958-06-16 1959-06-15
LU37336A1 (en) * 1958-06-27
BE595548A (en) * 1959-09-30

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3234198A (en) * 1962-12-10 1966-02-08 Shell Oil Co Polymerization process
DE1268394B (en) * 1964-04-30 1968-05-16 Huels Chemische Werke Ag Process for the preparation of mixtures of structurally uniform, high molecular weight 1,4-cis- and 1,4-trans-polybutadienes
DE1253918B (en) * 1964-06-06 1967-11-09 Japan Synthetic Rubber Co Ltd Process for the production of cis-1,4-polybutadiene
US3432517A (en) * 1964-06-06 1969-03-11 Japan Synthetic Rubber Co Ltd Method for polymerizing butadiene; a catalyst for use in said method and a method for producing the catalyst
DE1570827B1 (en) * 1964-12-07 1970-08-06 Internat Synthetic Rubber Comp Process for the preparation of cis-1,4-polybutadiene
DE1570293B1 (en) * 1965-07-13 1970-02-05 Bridgestone Tire Co Ltd Process for making copolymers of conjugated diolefins
DE2364805A1 (en) * 1972-12-27 1974-08-08 Sumitomo Chemical Co LIQUID SERVICE POLYMERIZES, PROCESS FOR THEIR PRODUCTION AND THEIR USE

Also Published As

Publication number Publication date
DE1570275A1 (en) 1970-03-12
DE1570275B2 (en) 1971-01-21
DE1213120B (en) 1966-03-24
FR1283371A (en) 1962-02-02
US3170907A (en) 1965-02-23

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